The present invention relates to herbicidal pyrrolesulfonylureas, compositions thereof and a method for their use as preemergence and/or postemergence herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,368,067 discloses herbicidal sulfonylureas of the formula ##STR1## wherein: R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CH, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5 or CO.sub.2 H;
R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA1 R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.6 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NR.sub.7 R.sub.8 ; and PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl. PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C(W)R.sub.8, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n --C.sub.1 -C.sub.3 alkyl or C(O)R.sub.9 ; PA1 R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, C(O)C.sub.1 -C.sub.4 alkoxy, C(O)NR.sub.6 R.sub.7 or C(O)C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms; PA1 R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sub.7 is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl; or PA1 R.sub.6 and R.sub.7, together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated heterocyclic ring which may contain an oxygen; and PA1 Y is O or S. PA1 R.sub.1 is H, halogen, NO.sub.2, CR.sub.6 (OC.sub.1 -C.sub.4 alkyl).sub.2, ##STR4## SO.sub.2 NR.sub.7 R.sub.8, C(O)R.sub.9 or (Y)mR.sub.10 ; X is O, S, NR.sub.5, C(R.sub.5).dbd.N, CH.dbd.CH or ##STR5## R.sub.5 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl. PA1 m is 0, 1 or 2; PA1 R.sup.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl or phenyl; and PA1 R.sup.10 and R.sup.11 are independently H or C.sub.1 -C.sub.4 alkyl. PA1 R.sup.1 is H; CH.sub.3 ; CH.sub.2 OCH.sub.3 ; CH.sub.2 OC.sub.2 H.sub.5 ; CH.sub.2 CN; CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5 ; C.sub.2 -C.sub.6 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; C.sub.3 -C.sub.4 haloalkenyl; C.sub.3 -C.sub.6 cycloalkyl; C(O)R.sup.5 ; N(CH.sub.3).sub.2 ; or Q.sup.1 ; PA1 R.sup.2 is C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; (CH.sub.2).sub.m Q.sup.2 ; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; C(R.sup.14)(OR.sup.15)(OR.sup.16); S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; NO.sub.2 ; halogen or OR.sup.73 ; PA1 R.sup.3 is H, halogen or C.sub.1 -C.sub.4 alkyl; PA1 R.sup.4 is H, C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; or halogen; PA1 R.sup.5 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NR.sup.20 R.sup.21 ; PA1 R.sup.6 is H, C.sub.1 -C.sub.2 alkyl or OCH.sub.3 ; PA1 R.sup.7 is C.sub.1 -C.sub.2 alkyl; or PA1 R.sup.6 and R.sup.7 can be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --; PA1 R.sup.8 is H, C.sub.1 -C.sub.3 alkyl or cyclopropyl; PA1 R.sup.9 is CH.sub.3 ; C.sub.2 -C.sub.3 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, OH, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or propargyl; PA1 R.sup.10 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ; PA1 R.sup.11 is C.sub.1 -C.sub.3 alkyl; or PA1 R.sup.10 and R.sup.11 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sup.12 is H, C.sub.1 -C.sub.3 alkyl, allyl, halogen, CN, N.sub.3, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or SCN; PA1 R.sup.13 is C.sub.1 -C.sub.3 alkyl or allyl; PA1 R.sup.14 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.15 and R.sup.16 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sup.17 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or cyclopropylmethyl; PA1 R.sup.18 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ; PA1 R.sup.19 is H or C.sub.1 -C.sub.2 alkyl; or PA1 R.sup.18 and R.sup.19 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; PA1 R.sup.20 and R.sup.21 are independently C.sub.1 -C.sub.2 alkyl; or PA1 R.sup.20 and R.sup.21 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sup.71 is H, halogen or CF.sub.3 ; PA1 R.sup.73 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogens, CN, C.sub.1 -C.sub.2 alkoxy, or C.sub.1 -C.sub.2 alkylthio; C(O)R.sup.74 ; SO.sub.2 R.sup.75 ; C.sub.3 -C.sub.4 alkenyl; or propargyl; PA1 R.sup.74 is C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy, one or more halogens, or CN; C.sub.3 -C.sub.4 alkenyl; or C.sub.1 -C.sub.3 alkoxy; PA1 R.sup.75 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 m is 0 or 1; PA1 n is 0, 1 or 2; PA1 Q.sup.1 is phenyl, phenyl substituted with one to two groups selected from halogen and CH.sub.3, a fully unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N and a fully unsaturated 5- or 6-membered heterocyclic ring substituted with one to two groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.3 -C.sub.4 alkenylthio and C.sub.1 -C.sub.2 haloalkylthio, said Q.sup.1 bound through a carbon atom; PA1 Q.sup.2 is phenyl, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O and 0-2 S, a partially saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N, a fully unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N, phenyl substituted with one to two groups selected from halogen and CH.sub.3, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O and 0-2 S substituted with one to two C.sub.1 -C.sub.3 alkyl groups, a partially saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N substituted with one to two C.sub.1 -C.sub.3 alkyl groups, and an unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N substituted with one to two groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.3 -C.sub.4 alkenylthio and C.sub.1 -C.sub.2 haloalkylthio; PA1 A is ##STR10## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR11## or N(OCH.sub.3)CH.sub.3 ; p is 2 or 3; PA1 Q.sup.3 and Q.sup.4 are independently O or S; PA1 R.sup.22 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.23 and R.sup.24 are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH or N; PA1 Z.sup.1 is CH or N; PA1 Y.sup.1 is O or CH.sub.2 ; PA1 X.sup.1 is CH.sub.3, OCH.sub.3 or OCF.sub.2 H; PA1 X.sup.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 Y.sup.2 is OCH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3, SCH.sub.2 CH.sub.3, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sup.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sup.3 is H or CH.sub.3 ; PA1 X.sup.4 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sup.4 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or Cl; PA1 (a) when X and/or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (b) when m is zero, Q.sup.2 is bound through carbon to the pyrrole ring in J; PA1 (c) when X is F, Cl, Br or I, then Z is CH and Y is OCH.sub.3, OCH.sub.2 CH.sub.3, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (d) when W is S, then R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.3, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 PA1 (f) when A is A-2, A-3, A-4, A-5, A-6 or A-7, then R is H; PA1 (g) when J is J-1, A is A-1 and X and/or Y is alkyl, then R.sup.2 is other than CN or NO.sub.2 ; PA1 (h) when J is J-1, A is A-2, A-3 or A-4 and R.sup.1 is C(O)R.sup.5, then R.sup.2 is other than alkyl; and PA1 (i) when J is J-1, A is A-1 and X and/or Y is C.sub.1 haloalkoxy, then R.sup.2 is other than C(O)OR.sup.9. PA1 R.sup.27 and R.sup.28 are independently H, F, or CH.sub.3 ; PA1 R.sup.29 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.30 is H or CH.sub.3 ; PA1 R.sup.31, R.sup.32 and R.sup.33 are independently H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.34, R.sup.35 and R.sup.36 are independently H, CH.sub.3, CH.sub.2 CH.sub.3, Cl, Br, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sup.37 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sup.38 is CH.sub.3 ; PA1 R.sup.39 is H, C.sub.1 -C.sub.2 alkyl, OCH.sub.3 or SCH.sub.3 ; PA1 R.sup.40 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sup.41 and R.sup.42 are independently H or CH.sub.3 ; PA1 R.sup.43 is H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.3 H.sub.7 ; PA1 W.sup.1 is O or S; PA1 W.sup.2 is O, S or NR.sup.44 ; PA1 R.sup.44 is H or CH.sub.3 ; PA1 Q.sup.2 is ##STR14## r is 0 or 1; R.sup.45 and R.sup.46 are independently H, CH.sub.3 or Cl; PA1 R.sup.47 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.48 is H or CH.sub.3 ; PA1 R.sup.49 and R.sup.50 are independently H or CH.sub.3 ; PA1 R.sup.51 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.52 is H or CH.sub.3 ; PA1 R.sup.53 R.sup.54 and R.sup.55 are independently H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.56, R.sup.57 and R.sup.58 are independently H, CH.sub.3, CH.sub.2 CH.sub.3, Cl, Br, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sup.59 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sup.60 is CH.sub.3 ; PA1 R.sup.61 is H, C.sub.1 -C.sub.2 alkyl, OCH.sub.3 or SCH.sub.3 ; PA1 R.sup.62 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sup.63 and R.sup.64 are independently H or CH.sub.3 ; PA1 R.sup.65 is H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.3 H.sub.7 ; PA1 W.sup.3 is O or S; PA1 W.sup.4 is O, S or NR.sup.66 ; and PA1 R.sup.66 is H or CH.sub.3. PA1 W is O; PA1 R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, allyl, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 SCH.sub.3 phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C(O)OCH.sub.3 or C(O)N(CH.sub.3).sub.2 ; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sup.22, ##STR15## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3. PA1 R.sup.3 is H, CH.sub.3, Cl or Br; and PA1 R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl or Br; PA1 R.sup.8 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sup.9 is C.sub.1 -C.sub.2 alkyl or CH.sub.2 CH.sub.2 Cl; PA1 R.sup.10 is H or CH.sub.3 ; PA1 R.sup.11 is CH.sub.3 ; PA1 R.sup.12 is H, CH.sub.3, C.sub.2 H.sub.5 or Cl; PA1 R.sup.13 is CH.sub.3 ; PA1 R.sup.14 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sup.15 and R.sup.16 are CH.sub.3 ; PA1 R.sup.17 is C.sub.1 -C.sub.2 alkyl; PA1 R.sup.18 is H or CH.sub.3 ; PA1 R.sup.19 is CH.sub.3 ; and PA1 n is 0 or 2. PA1 R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl, Br or OR.sup.73. PA1 R is H; and PA1 R.sup.71 is H. PA1 J is J-1. PA1 J is J-2. PA1 J is J-3. PA1 R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ; PA1 R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5 or S(O).sub.2 N(CH.sub.3).sub.2 ; PA1 R.sup.8 is C.sub.1 -C.sub.2 alkyl; PA1 R.sup.9 is C.sub.1 -C.sub.2 alkyl; PA1 Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21; PA1 R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H; PA1 R.sup.65 is CH.sub.3 ; PA1 W.sup.3 is S; and PA1 r is 0. PA1 R.sup.2 is C.sub. -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ; PA1 R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ; PA1 R.sup.8 is C.sub.1 -C.sub.2 alkyl; PA1 R.sup.9 is C.sub.1 -C.sub.2 alkyl; PA1 Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21; PA1 R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H; PA1 R.sup.65 is CH.sub.3 ; PA1 W.sup.3 is S; and PA1 r is 0. PA1 R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ; PA1 R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ; PA1 R.sup.8 is C.sub.1 -C.sub.2 alkyl; PA1 R.sup.9 is C.sub.1 -C.sub.2 alkyl; PA1 Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21; PA1 R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H; PA1 R.sup.65 is CH.sub.3 ; PA1 W.sup.3 is S; and PA1 r is 0. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and PA1 Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and PA1 Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and PA1 Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2. PA1 R.sup.72 is H or Si(CH(CH.sub.3).sub.2).sub.3. PA1 (a) the compounds of Equation 1 in an inert polar aprotic solvent for 5 minutes to 24 hours or more at 20.degree. to 80.degree. C. ##STR17## (b) the compounds of Equation 2 in an inert solvent followed by treatment with aqueous acid ##STR18## (c) the compounds of Equation 3 in an inert solvent for 0.5 to 24 hours ##STR19## (d) the compounds of Equation 4 in an inert solvent at 20.degree. to 80.degree. C. for 0.5 to 24 hours and in the presence of 1 to 1.4 equivalents of a base ##STR20##
U.S. Pat. No. 4,549,898 discloses herbicidal sulfonamides of the formula ##STR2## wherein: X is O, S, NR.sub.4 or --C(R.sub.5).dbd.N--;
EP-A-126,711 discloses herbicidal sulfonamides of the formula ##STR3## wherein: Q is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2, NH.sub.2, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, CN, C.sub.1 -C.sub.4 alkoxycarbonyl, CHO, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl;
EP-A-161,211 discloses herbicidal sulfonamides of the formula ##STR6## wherein: G is ##STR7## R.sup.2 is ##STR8## Q is O, S or NR.sup.7 ; A is O, S, SO, SO.sub.2 or --(CR.sub.10 R.sub.11).sub.m --;